Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 17, Pages 4197-4203Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100676
Keywords
Asymmetric catalysis; [4+3]-Cycloaddition; Azaoxyallyl cation; Benzodiazepinone; Peripheral nerve degeneration
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Funding
- Basic Science Research Program through the National Research Foundation of Korea (NRF) - Ministry of Education [NRF-2018R1D1A1B07040282, NRF-2020R1A2C1005438]
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The first organocatalytic asymmetric [4+3]-cycloaddition of 2-aminophenyl alpha,beta-unsaturated carbonyls with in situ generated azaoxyallyl cations was successfully developed, leading to the synthesis of enantioenriched functionalized seven-membered 1,4-benzodiazepine-3-ones. This method was also extended to the first asymmetric [4+3]-cycloaddition of delta-hydroxy alpha,beta-unsaturated carbonyls, providing 1,4-oxazepanes in one step under mild conditions. Some of the novel adducts showed promising bioactivity in preventing peripheral nerve degeneration.
The first organocatalytic asymmetric [4+3]-cycloaddition of 2-aminophenyl alpha,beta-unsaturated carbonyls with in situ generated azaoxyallyl cations was developed, and enantioenriched functionalized seven-membered 1,4-benzodiazepine-3-ones were obtained in good yields and with excellent enantioselectivities. This approach was also extended to the first asymmetric [4+3]-cycloaddition of delta-hydroxy alpha,beta-unsaturated carbonyls, affording 1,4-oxazepanes in one step under mild conditions. Several of the novel adducts demonstrated promising bioactivity in the prevention of peripheral nerve degeneration.
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